KR101413076B1 - Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film - Google Patents
Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film Download PDFInfo
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- KR101413076B1 KR101413076B1 KR1020110141439A KR20110141439A KR101413076B1 KR 101413076 B1 KR101413076 B1 KR 101413076B1 KR 1020110141439 A KR1020110141439 A KR 1020110141439A KR 20110141439 A KR20110141439 A KR 20110141439A KR 101413076 B1 KR101413076 B1 KR 101413076B1
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
Abstract
(A) an alkali-soluble resin prepared from a phosphorus-containing diamine represented by the following formula (1), (B) a photosensitive diazoquinone compound and (C) a solvent, a photosensitive resin film prepared using the same, A semiconductor device comprising the photosensitive resin film is provided.
[Chemical Formula 1]
(Wherein each substituent is as defined in the specification).
Description
The present invention relates to a positive photosensitive resin composition, a photosensitive resin film produced using the positive photosensitive resin composition, and a semiconductor device comprising the photosensitive resin film.
As the insulating film material of the organic light emitting display, polyimide resin is excellent in heat resistance, stable even at a temperature of 200 占 폚 or more, excellent in mechanical strength, low dielectric constant and planarization property of coating surface, It is in the spotlight because it can easily realize a fine pattern with a low inclusion content.
The fabrication of an insulating film or a semiconductor protective film of an organic light emitting display device using a conventional polyimide resin involves a further photoresist process and is a complicated process using a method of etching with an organic solvent after patterning, It may cause environmental problems due to use, and also cause a problem that the resist pattern is swollen.
On the other hand, when forming a pixel crystal layer of a semiconductor circuit protective film or an organic light emitting display device, a dry etching technique may be used to remove organic substances remaining in the exposed portion. In this case, it is necessary to selectively remove the residue of the pattern portion exposed by dry etching. For this purpose, research is being conducted on a resin material which is less influenced by the etching of the non-exposed portion in the dry etching process.
Further, in order to realize excellent etching resistance, it is required to increase the carbon content of the resin. In this case, there is a problem that the resin must be exposed at a high temperature of 400 ° C or higher in the process.
One embodiment of the present invention is to provide a positive photosensitive resin composition that is excellent in photosensitivity, has a high residue removal ratio in the exposed area, and is excellent in etching resistance and heat resistance.
Another embodiment of the present invention is to provide a photosensitive resin film produced using the above positive photosensitive resin composition.
Another embodiment of the present invention is to provide a semiconductor device comprising the photosensitive resin film.
(A) an alkali-soluble resin prepared from a phosphorus-containing diamine represented by the following formula (1); (B) a photosensitive diazoquinone compound; And (C) a solvent.
[Chemical Formula 1]
(In the formula 1,
R ' and R " each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 hetero A substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group,
R represents a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 A substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group,
n ' and n " are each an integer of 0 to 3.)
The phosphorus-containing diamine may include at least one selected from the compounds represented by the following general formulas (2) and (3).
(2)
(3)
The alkali-soluble resin may include a polybenzoxazole precursor including a repeating unit represented by the following general formula (4).
[Chemical Formula 4]
(In the formula 4,
X 1 is a residue derived from the phosphorus-containing diamine represented by the above formula (1)
Y 1 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic group.
The alkali-soluble resin may be prepared from the phosphorus-containing diamine and the aromatic diamine, and the aromatic diamine may include at least one selected from the following formulas (8) and (9).
[Chemical Formula 8]
[Chemical Formula 9]
(In the above formulas 8 and 9,
A is a single bond, -O-, -CO-, -CR 4 R 5 -, -SO 2 - or -S-, R 4 and R 5 are each independently a hydrogen atom or a substituted or unsubstituted C1 To C30 alkyl group,
R 1 to R 3 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted C1 to C30 carboxyl group, a hydroxyl group or a thiol group,
n 1 is an integer of 0 to 2,
n 2 and n 3 are each an integer of 0 to 3.)
The phosphorus-containing diamine and the aromatic diamine may be mixed in a weight ratio of 5:95 to 95: 5.
The alkali-soluble resin may include a polybenzoxazole precursor including repeating units represented by the following formulas (4) and (10).
[Chemical Formula 4]
(In the formula 4,
X 1 is a residue derived from the phosphorus-containing diamine represented by the above formula (1)
Y 1 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic group.
[Chemical formula 10]
(In the formula (10)
X 2 is a residue derived from an aromatic diamine containing at least one selected from the above formulas (8) and (9)
Y 2 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic group.
The positive photosensitive resin composition may further comprise an alkali soluble resin prepared from (A ') an aromatic diamine, and the aromatic diamine may include at least one selected from the formulas (8) and (9).
The alkali-soluble resin (A) prepared from the phosphorus-containing diamine and the alkali-soluble resin (A ') prepared from the aromatic diamine may be mixed at a weight ratio of 5:95 to 95: 5.
The alkali-soluble resin may have a weight average molecular weight (Mw) of 3,000 to 300,000 g / mol.
The positive photosensitive resin composition may contain 5 to 100 parts by weight of the photosensitive diazoquinone compound (B) and 100 to 900 parts by weight of the solvent (C), based on 100 parts by weight of the alkali-soluble resin (A).
Another embodiment of the present invention provides a photosensitive resin film produced using the positive photosensitive resin composition.
Another embodiment of the present invention provides a semiconductor device comprising the photosensitive resin film.
Other details of the embodiments of the present invention are included in the following detailed description.
The positive photosensitive resin composition is excellent in photosensitivity, has a high residue removal rate in the exposed area, and is excellent in resistance to etching and heat resistance, and thus can be usefully used for a pixel circuit layer of a semiconductor circuit protection film or an organic light emitting display device.
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (-F, -Cl, -Br or -I), a hydroxy group, a nitro group, An amino group (NH 2 , NH (R 200 ) or N (R 201 ) (R 202 ) in which R 200 , R 201 and R 202 are the same or different from each other and are each independently a Cl to C10 alkyl group) A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, A substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
Unless otherwise specified in the specification, "alkyl group" means C1 to C30 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C30 cycloalkyl group, specifically C3 Refers to a C1 to C30 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C30 aryl group, specifically, a C6 to C30 aryl group, C18 aryl group, "alkenyl group" means C2 to C30 alkenyl group, specifically C2 to C18 alkenyl group, "alkylene group" means C1 to C30 alkylene group, specifically C1 Means a C6 to C30 arylene group, and specifically refers to a C6 to C16 arylene group.
Unless otherwise specified in the present specification, the term "aliphatic organic group" means a C1 to C30 alkyl group, a C2 to C30 alkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkylene group, a C2 to C30 alkenylene group, Means a C1 to C15 alkyl group, a C2 to C15 alkenyl group, a C2 to C15 alkynyl group, a C1 to C15 alkylene group, a C2 to C15 alkenylene group, or a C2 to C15 alkynylene group, Means a C3 to C30 cycloalkyl group, a C3 to C30 cycloalkenyl group, a C3 to C30 cycloalkynyl group, a C3 to C30 cycloalkylene group, a C3 to C30 cycloalkenylene group, or a C3 to C30 cycloalkynylene group. C3 to C15 cycloalkenyl groups, C3 to C15 cycloalkynyl groups, C3 to C15 cycloalkylene groups, C3 to C15 cycloalkenylene groups, Means a C6 to C30 aryl group or a C6 to C30 arylene group, specifically, a C6 to C16 aryl group or a C6 to C16 arylene group, and the term " aromatic hydrocarbon group " The "heterocyclic group" means a C2 to C30 heterocycloalkyl group containing 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si and combinations thereof in one ring, C2 to C30 hetero A C2 to C30 heterocycloalkenyl group, a C2 to C30 heterocycloalkenylene group, a C2 to C30 heterocycloalkynyl group, a C2 to C30 heterocycloalkynylene group, a C2 to C30 heteroaryl group, or a C2 to C30 hetero Means an arylene group, and specifically includes 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si, and combinations thereof in one ring A C2 to C15 heterocycloalkylene group, a C2 to C15 heterocycloalkylene group, a C2 to C15 heterocycloalkenyl group, a C2 to C15 heterocycloalkenylene group, a C2 to C15 heterocycloalkynyl group, a C2 to C15 heterocycloalkynylene group, a C2 to C15 heterocycloalkylene group, To C15 heteroaryl groups, or C2 to C15 heteroarylene groups.
As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization, random copolymerization or graft copolymerization, and "copolymer" means block copolymer, random copolymer or graft copolymer.
In the present specification, "*" means the same or different atom or part connected to a chemical formula.
The positive photosensitive resin composition according to one embodiment includes (A) an alkali-soluble resin, (B) a photosensitive diazoquinone compound, and (C) a solvent.
Each component will be described in detail below.
(A) an alkali-soluble resin
The alkali-soluble resin may be prepared from a phosphorus-containing diamine represented by the following general formula (1).
[Chemical Formula 1]
In the general formula (1), R ' and R " are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, Or a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group.
Wherein R is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 alkoxy group, Or a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, A substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group. Of these, preferably a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.
In the above formula (1), n ' and n '' may each be an integer of 0 to 3.
The hydroxy group present in the above formula (1) is a functional group which reacts upon curing, and the amino group may react upon polymerization to obtain polyhydroxyamide as a polybenzoxazole precursor. Also, since the hydroxy group and the amino group are present at ortho positions with respect to each other, cyclic benzoxazole structures can be formed by ring closure upon curing.
When the alkali-soluble resin, specifically the polybenzoxazole precursor, is prepared by adding the phosphorus-containing diamine represented by the above formula (1), the obtained positive photosensitive resin composition has excellent photosensitivity, and the residual removal rate of the exposed portion in the pattern- High etching resistance and heat resistance.
The phosphorus-containing diamine may specifically include at least one selected from the compounds represented by the following general formulas (2) and (3).
(2)
(3)
The alkali-soluble resin may be a polybenzoxazole precursor containing a repeating unit represented by the following formula (4) prepared from the phosphorus-containing diamine.
[Chemical Formula 4]
In Formula 4 X 1 is can be a glass derived from a phosphorus-containing diamine of the formula (1).
In Formula 4, Y 1 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic organic group . Specifically, Y 1 may be a residue of a dicarboxylic acid or a residue of a dicarboxylic acid derivative.
Examples of the dicarboxylic acids may be mentioned Y 1 (COOH) 2 (where Y 1 is the same as Y 1 in the formula (6)).
Examples of the di-carboxylic acid derivatives is Y 1 (COOH) 2 of the carbonyl halide derivative, or Y 1 (COOH) 2 and 1-hydroxy-1,2,3-benzotriazole-active ester derivative by reacting a sol such as Active compounds.
Specific examples of the dicarboxylic acid derivative include 4,4'-oxydibenzoyl chloride, diphenyloxydicarbonyldichloride, bis (phenylcarbonyl chloride) sulfone, bis (phenylcarbonyl chloride) ether, bis (phenylcarbonyl chloride ) Phenone, phthaloyldichloride, terephthaloyldichloride, isophthaloyldichloride, dicarbonyldichloride, diphenyloxydicarboxylate dibenzotriazole, or combinations thereof, but is not limited thereto.
Examples of Y 1 include functional groups represented by the following formulas (5) to (7), but are not limited thereto.
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the general formulas (5) to (7), R 10 to R 13 may each independently be a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, n 4 , n 6 and n 7 may each be an integer of 0 to 4, and n 5 may be an integer of 0 to 3.
In the general formulas 5 to 7, A 2 may be a single bond, O, CR 4 R 5 , CO, CONH, S or SO 2 , wherein R 4 and R 5 are each independently a hydrogen atom, C30 alkyl group, and specifically may be a C1 to C30 fluoroalkyl group.
The alkali-soluble resin may be prepared by mixing the phosphorus-containing diamine and the aromatic diamine together.
The aromatic diamine may be at least one selected from the following formulas (8) and (9).
[Chemical Formula 8]
[Chemical Formula 9]
In Formulas 8 and 9, A may be a single bond, -O-, -CO-, -CR 4 R 5 -, -SO 2 - or -S-, wherein R 4 and R 5 are each independently hydrogen Atom, or a substituted or unsubstituted C1 to C30 alkyl group. Of these, preferably -CR 4 R 5 -, wherein R 4 and R 5 may each be a C1 to C30 fluoroalkyl group.
In formulas (8) and (9), R 1 to R 3 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted C1 to C30 carboxyl group, a hydroxyl group or a thiol group.
In the general formulas (8) and (9), n 1 may be an integer of 0 to 2, and n 2 and n 3 may each be an integer of 0 to 3.
Specific examples of the aromatic diamine include 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, bis (4-amino-3-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone, bis , 2,2-bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane, 2,2- ) -1,1,1,3,3,3-hexafluoropropane, 2,2-bis (3-amino-4-hydroxy-5-trifluoromethylphenyl) hexafluoropropane, 2,2- (3-amino-4-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2,2-bis Hexafluoropropane, 2,2-bis (4-amino-3-hydroxy-6-trifluoromethylphenyl) hexa Flu (4-amino-3-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2,2-bis Hydroxyphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- 2- (3-amino-5-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- 2- (3-amino-4-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2- 2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane, 2- (3- Amino-4-hydroxy-6-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane, or a combination thereof. It is not.
The phosphorus-containing diamine and the aromatic diamine may be mixed in a weight ratio of 5:95 to 95: 5, specifically 5:95 to 50:50. When mixed in the above weight ratio range, a positive photosensitive resin composition having excellent photosensitivity and high residue removal ratio at the exposed portion in the pattern forming process and excellent in etching resistance and heat resistance can be obtained.
The alkali-soluble resin may be a polybenzoxazole precursor prepared from the phosphorus-containing diamine and the aromatic diamine.
The polybenzoxazole precursor may include a repeating unit represented by the formula (4) and a repeating unit represented by the following formula (10).
[Chemical formula 10]
In formula (10), X 2 may be a residue derived from an aromatic diamine containing at least one selected from the formulas (8) and (9). The aromatic diamine is as described above.
Wherein Y 2 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic organic group . And Y < 2 > is the same as defined in Y < 1 >
The alkali-soluble resin prepared from the phosphorus-containing diamine represented by the formula (1) may be mixed with an alkali-soluble resin prepared from at least one aromatic diamine selected from the formulas (8) and (9).
The alkali-soluble resin prepared from the phosphorus-containing diamine and the alkali-soluble resin prepared from the aromatic diamine can be mixed in a weight ratio of 5:95 to 95: 5, specifically, in a weight ratio of 5:95 to 50:50 . When mixed in the above weight ratio range, a positive photosensitive resin composition having excellent photosensitivity and high residue removal ratio at the exposed portion in the pattern forming process and excellent in etching resistance and heat resistance can be obtained.
The alkali-soluble resin may have a weight average molecular weight (Mw) of 3,000 to 300,000 g / mol, and more specifically, a weight average molecular weight (Mw) of 5,000 to 20,000 g / mol. When the weight average molecular weight (Mw) is within the above range, a sufficient residual film ratio can be obtained in an unexposed area at the time of development with an aqueous alkali solution, and patterning can be efficiently performed.
(B) Photosensitive Diazoquinone compound
The photosensitive diazoquinone compound may be a compound having a 1,2-benzoquinone diazide structure or a 1,2-naphthoquinone diazide structure.
The photosensitive diazoquinone compound may be at least one selected from compounds represented by the following general formulas (11) and (13) to (15), but is not limited thereto.
(11)
In the formula (11), R 14 to R 16 each independently represent a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, and specifically may be a methyl group.
In Formula 11, R 17 to R 19 may each independently be OQ, and Q may be a hydrogen atom, a functional group represented by Formula 12a, or a functional group represented by Formula 12b, There is no.
In Formula 11, n 8 to n 10 may each be an integer of 0 to 3.
[Chemical Formula 12a]
[Chemical Formula 12b]
[Chemical Formula 13]
In Formula 13, R 20 may be a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, R 21 to R 23 may each independently be OQ, Q is the same as defined in Formula 11 , n 11 To n < 13 > may each be an integer of 0 to 3.
[Chemical Formula 14]
In Formula 14, A 3 may be CO or CR 4 R 5 , and R 4 And R < 5 > may each independently be a substituted or unsubstituted C1 to C30 alkyl group.
In the formula (14), R 24 to R 27 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, OQ or NHQ, and Q is the same as defined in the above formula (11).
In Formula 14, n 14 to n 17 may each be an integer of 0 to 4, and n 14 + n 15 and n 16 + n 17 may each be an integer of 5 or less.
Provided that at least one of R 24 and R 25 may be OQ, one to three OQs may be contained in one aromatic ring, and one to four OQs may be contained in another aromatic ring.
[Chemical Formula 15]
In Formula 15,
R 28 to R 35 each independently may be a hydrogen atom, or a substituted or unsubstituted C1 to C30 alkyl group, n 18 and n 19 may be an integer from 1 to 5, respectively, Q is as defined in the formula (11) same.
The photosensitive diazoquinone compound may be included in the positive photosensitive resin composition in an amount of 5 to 100 parts by weight, specifically 10 to 50 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When it is included in the above range, the pattern can be formed well with no residue by exposure, and a good pattern can be obtained without loss of film thickness upon development.
(C) Solvent
The positive photosensitive resin composition may include a solvent capable of easily dissolving each component.
Specific examples of the solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, Alkylene glycol alkyl ethers such as propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and 1,3-butylene glycol-3-monomethyl ether; alkyl acetates such as propyl acetate, butyl acetate and isobutyl acetate; Ketones such as acetyl acetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone and cyclopentanone; alcohols such as butyl alcohol, isobutyl alcohol, pentanol and 4-methyl- Aromatic hydrocarbons such as N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, Propyleneglycol monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 3-methyl-3 But are not limited to, methoxybutyl acetate, methyl pyruvate, ethyl pyruvate, methyl-3-methoxy propionate, and combinations thereof. These solvents may be used alone or in combination of two or more.
The solvent may be appropriately selected and used depending on the step of forming a photosensitive resin film such as spin coating, slit die coating and the like.
The solvent may be included in the positive photosensitive resin composition in an amount of 100 to 900 parts by weight, specifically 300 to 800 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When it is contained within the above range, it is possible to coat a film of sufficient thickness, and it can have excellent solubility and coating property.
Specifically, the solvent may be used so that the solid content of the positive photosensitive resin composition is 5 to 50% by weight.
(D) Other additives
The positive photosensitive resin composition according to one embodiment may further include other additives.
Other additives include thermal latent acid generators. Examples of the thermal latent acid generator include arylsulfonic acids such as p-toluenesulfonic acid, benzenesulfonic acid and the like; Perfluoroalkylsulfonic acids such as trifluoromethanesulfonic acid, trifluorobutanesulfonic acid and the like; Methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid and the like; Or combinations thereof, but are not limited thereto.
The thermal latent acid generator is a catalyst for the dehydration reaction of the phenolic hydroxyl group-containing polyamide of the polybenzoxazole precursor and the cyclization reaction, and the cyclization reaction can proceed smoothly even if the curing temperature is lowered.
Further, a suitable surfactant or leveling agent may be further used as an additive in order to prevent unevenness in film thickness or to improve developability.
The step of forming a pattern using the positive photosensitive resin composition includes a step of applying a positive photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied positive photosensitive resin composition to form a positive photosensitive resin composition film; Exposing the positive photosensitive resin composition film; A step of developing the exposed positive photosensitive resin composition film with an alkali aqueous solution to prepare a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The conditions of the process for forming the pattern, and the like are well known in the art, so that detailed description thereof will be omitted herein.
According to another embodiment, there is provided a photosensitive resin film produced using the positive photosensitive resin composition. The photosensitive resin film may be used as an insulating film, a buffer film, or a protective film.
According to another embodiment, there is provided a semiconductor device comprising the photosensitive resin film. The semiconductor device may be an organic light emitting diode (OLED) or a liquid crystal display device (LCD).
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are for illustrative purposes only and are not intended to limit the present invention.
( Polybenzoxazole Precursor preparation)
Manufacturing example One
A four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas inlet and a condenser was charged with nitrogen 11.0 g of bis (3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide was dissolved in 280 g of N-methyl-2-pyrrolidone (NMP). When the solid is completely dissolved, 9.9 g of pyridine is added to the solution, and 13.3 g of 4,4'-oxydibenzoyl chloride is added to 142 g of N-methyl-2-pyrrolidone (NMP) Was slowly added dropwise for 30 minutes. After the dropwise addition, the reaction was carried out at 0 to 5 ° C for 1 hour, the temperature was raised to room temperature, and the reaction was terminated by stirring for 1 hour. To this was added 1.6 g of 5-norbornene-2,3-dicarboxyanhydride and the mixture was stirred at 70 ° C for 24 hours to complete the reaction. The reaction mixture was poured into a solution of water / methanol = 10/1 (volume ratio) to form a precipitate, and the precipitate was filtered and sufficiently washed with water. The polybenzoxazole precursor having a weight average molecular weight of 8,100 g / mol was prepared by drying at 80 캜 under vacuum for 24 hours or more.
Manufacturing example 2
(3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide instead of 11.0 g of bis (3-amino-4-hydroxyphenyl) -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was used instead of the polybenzoxazole Precursor. The weight average molecular weight of the polybenzoxazole precursor is 9,500 g / mol.
Manufacturing example 3
(3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide was obtained in the same manner as in Production Example 1, except that 11.0 g of bis (3-amino-4-hydroxyphenyl) Except that 15.5 g of bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. Wherein the polybenzoxazole precursor has a weight average molecular weight of 9,400 g / mol.
Manufacturing example 4
(3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide instead of 11.0 g of bis (3-amino-4-hydroxyphenyl) -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. The weight average molecular weight of the polybenzoxazole precursor is 9,500 g / mol.
Manufacturing example 5
(3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide instead of 11.0 g of bis (3-amino-4-hydroxyphenyl) -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. Wherein the polybenzoxazole precursor has a weight average molecular weight of 8,700 g / mol.
Manufacturing example 6
(3-amino-4-hydroxyphenyl) (phenyl) phosphine oxide instead of 11.0 g of bis (3-amino-4-hydroxyphenyl) -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added to a solution of polybenzoxazole Precursor. The weight average molecular weight of the polybenzoxazole precursor is 8,600 g / mol.
Manufacturing example 7
A four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas inlet and a condenser was charged with nitrogen 9.5 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide was dissolved in 280 g of N-methyl-2-pyrrolidone (NMP). When the solid is completely dissolved, 9.9 g of pyridine is added to the solution, and 13.3 g of 4,4'-oxydibenzoyl chloride is added to 142 g of N-methyl-2-pyrrolidone (NMP) Was slowly added dropwise for 30 minutes. After the dropwise addition, the reaction was carried out at 0 to 5 ° C for 1 hour, the temperature was raised to room temperature, and the reaction was terminated by stirring for 1 hour. To this was added 1.6 g of 5-norbornene-2,3-dicarboxyanhydride and the mixture was stirred at 70 ° C for 24 hours to complete the reaction. The reaction mixture was poured into a solution of water / methanol = 10/1 (volume ratio) to form a precipitate, and the precipitate was filtered and sufficiently washed with water. The polybenzoxazole precursor having a weight average molecular weight of 8,000 g / mol was prepared by drying at 80 캜 under vacuum for 24 hours or more.
Manufacturing example 8
Instead of 9.5 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide in Production Example 7, 0.5 g of bis (3-amino- -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was used instead of the polybenzoxazole Precursor. Wherein the polybenzoxazole precursor has a weight average molecular weight of 9,400 g / mol.
Manufacturing example 9
2.4 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide and 2.4 g of 2,2-bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide were used in place of 9.5 g of bis -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. Wherein the polybenzoxazole precursor has a weight average molecular weight of 9,300 g / mol.
Manufacturing example 10
(Ethyl) phosphine oxide was used instead of 9.5 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide in Production Example 7, -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. The weight average molecular weight of the polybenzoxazole precursor is 8,900 g / mol.
Manufacturing example 11
Instead of 9.5 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide in Production Example 7, 7.1 g of bis (3-amino- -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added as a polymerization initiator in the same manner as in Production Example 7, Precursor. The weight average molecular weight of the polybenzoxazole precursor is 8,500 g / mol.
Manufacturing example 12
(Ethyl) phosphine oxide instead of 9.5 g of bis (3-amino-4-hydroxyphenyl) (ethyl) phosphine oxide in Production Example 7 and 9.0 g of 2,2 -Bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added in place of the polybenzoxazole Precursor. The polybenzoxazole precursor had a weight average molecular weight of 8,400 g / mol.
Manufacturing example 13
A four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas inlet and a condenser was charged with nitrogen 20.6 g of 2,2-bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane was added to 280 g of N-methyl-2-pyrrolidone And dissolved. When the solid is completely dissolved, 9.9 g of pyridine is added to the solution, and 13.3 g of 4,4'-oxydibenzoyl chloride is added to 142 g of N-methyl-2-pyrrolidone (NMP) Was slowly added dropwise for 30 minutes. After the dropwise addition, the reaction was carried out at 0 to 5 ° C for 1 hour, the temperature was raised to room temperature, and the reaction was terminated by stirring for 1 hour. To this was added 1.6 g of 5-norbornene-2,3-dicarboxyanhydride and the mixture was stirred at 70 ° C for 24 hours to complete the reaction. The reaction mixture was poured into a solution of water / methanol = 10/1 (volume ratio) to form a precipitate, and the precipitate was filtered and sufficiently washed with water. The polybenzoxazole precursor having a weight average molecular weight of 10,200 g / mol was prepared by drying at 80 캜 under vacuum for at least 24 hours.
(Preparation of positive-type photosensitive resin composition)
Example One
10 g of the polybenzoxazole precursor obtained in Preparation Example 1 was added to and dissolved in 35.0 g of? -Butyrolactone (GBL), and then 1 g of the photosensitive diazoquinone represented by the following Chemical Formula 16 and 1 g of trimethoxy [ 0.02 g of 3- (phenylamino) propyl] silane, and 0.75 g of a phenol compound represented by the following formula (18) were dissolved and filtered through a 0.45 占 퐉 fluorine resin filter to prepare a positive photosensitive resin composition.
[Chemical Formula 16]
[Chemical Formula 17]
[Chemical Formula 18]
Example 2 to 12
A positive photosensitive resin composition was prepared in the same manner as in Example 1 except that 10 g of each of the polybenzoxazole precursors obtained in Production Examples 2 to 12 was used instead of 10 g of the polybenzoxazole precursor obtained in Production Example 1 .
Example 13
The procedure of Example 1 was repeated except that 0.5 g of the polybenzoxazole precursor obtained in Preparation Example 1 and 9.5 g of the polybenzoxazole precursor obtained in Preparation Example 13 were used instead of 10 g of the polybenzoxazole precursor obtained in Preparation Example 1 Thereby preparing a positive photosensitive resin composition.
Example 14
Except that 10 g of the polybenzoxazole precursor obtained in Preparation Example 1 was replaced by 5 g of the polybenzoxazole precursor obtained in Preparation Example 1 and 5 g of the polybenzoxazole precursor obtained in Preparation Example 13 instead of 10 g of the polybenzoxazole precursor obtained in Preparation Example 1 Thereby preparing a positive photosensitive resin composition.
Example 15
The procedure of Example 1 was repeated except that 9.5 g of the polybenzoxazole precursor obtained in Preparation Example 1 and 0.5 g of the polybenzoxazole precursor obtained in Preparation Example 13 were used instead of 10 g of the polybenzoxazole precursor obtained in Preparation Example 1, Thereby preparing a positive photosensitive resin composition.
Example 16
The procedure of Example 1 was repeated except that 0.5 g of the polybenzoxazole precursor obtained in Production Example 7 and 9.5 g of the polybenzoxazole precursor obtained in Production Example 13 were used instead of 10 g of the polybenzoxazole precursor obtained in Production Example 7 Thereby preparing a positive photosensitive resin composition.
Example 17
Except that 10 g of the polybenzoxazole precursor obtained in Production Example 7 was replaced by 5 g of the polybenzoxazole precursor obtained in Production Example 7 and 5 g of the polybenzoxazole precursor obtained in Production Example 13, Thereby preparing a positive photosensitive resin composition.
Example 18
The procedure of Example 1 was repeated except that 9.5 g of the polybenzoxazole precursor obtained in Preparation Example 7 and 0.5 g of the polybenzoxazole precursor obtained in Preparation Example 13 were used instead of 10 g of the polybenzoxazole precursor obtained in Preparation Example 7, Thereby preparing a positive photosensitive resin composition.
Comparative Example One
A positive photosensitive resin composition was prepared in the same manner as in Example 1, except that the polybenzoxazole precursor obtained in Preparation Example 1 was used instead of the polybenzoxazole precursor 10 g.
Evaluation 1: Measurement of thickness variation
The positive photosensitive resin composition prepared in Examples 1 to 18 and Comparative Example 1 was coated on an 8-inch wafer by using a spin coater made by Mikasa (1H-DX2), and then coated on a hot plate at 130 캜 for 2 minutes To form a photosensitive polybenzoxazole precursor film.
The polybenzoxazole precursor film was exposed to an I-line stepper (NSR i10C) manufactured by Nikon Corporation using a mask having a pattern of various sizes, and then exposed to 2.38% aqueous tetramethylammonium hydroxide solution at room temperature for 40 seconds, The exposed portion was dissolved and removed through a puddle, followed by washing with pure water for 30 seconds. Subsequently, the obtained pattern was cured at an oxygen concentration of 1000 ppm or less and at 150 占 폚 for 30 minutes and then at 320 占 폚 for 30 minutes by using an electric furnace to prepare a patterned film.
The film thickness change after the coating, development, curing and etching at the time of the film production was measured using a KMAC (ST4000-DLX) equipment, and the results are shown in Table 1 below.
Evaluation 2: Sensitivity measurement
In Evaluation 1, the exposure time in which a 10um L / S pattern was formed with a line width of 1: 1 after exposure and development in the film production was obtained and the sensitivity was measured as the optimum exposure time. The results are shown in Table 1 below.
Evaluation 3: 5% weight reduction Temperature measurement
In the evaluation 1, the dry etching of the film was carried out using CHF 3 / CF 4 mixed gas. The 5% weight reduction temperature was measured by thermogravimetric analyzer (TGA) at a temperature of 10 ° C. per minute And the weight change value was measured. The results are shown in Table 1 below.
Through Table 1, in Examples 1 to 18 using an alkali-soluble resin prepared from phosphorus-containing diamine according to one embodiment, compared with Comparative Example 1 using an alkali-soluble resin prepared from other kinds of aromatic diamines Thus, it can be confirmed that it is excellent in photosensitivity, has a high residue removal rate in the exposed area, and is excellent in etching resistance and heat resistance. Accordingly, it can be seen that it can be effectively used for a pixel circuit layer of a semiconductor circuit protection film or an organic light emitting display.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, and that various changes and modifications may be made without departing from the scope of the invention. It is natural to belong.
Claims (12)
(B) a photosensitive diazoquinone compound; And
(C) Solvent
Wherein the positive photosensitive resin composition is a positive photosensitive resin composition.
[Chemical Formula 1]
(In the formula 1,
R ' and R " each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 hetero A substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group,
R represents a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 A substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group,
n ' and n " are each an integer of 0 to 3.)
Wherein the phosphorus-containing diamine comprises at least one selected from compounds represented by the following general formulas (2) and (3).
(2)
(3)
Wherein the alkali-soluble resin comprises a polybenzoxazole precursor comprising a repeating unit represented by the following formula (4).
[Chemical Formula 4]
(In the formula 4,
X 1 is a residue derived from the phosphorus-containing diamine represented by the above formula (1)
Y 1 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic group.
The alkali-soluble resin is prepared from the phosphorus-containing diamine and the aromatic diamine,
Wherein the aromatic diamine comprises at least one selected from the following formulas (8) and (9).
[Chemical Formula 8]
[Chemical Formula 9]
(In the above formulas 8 and 9,
A is a single bond, -O-, -CO-, -CR 4 R 5 -, -SO 2 - or -S-, R 4 and R 5 are each independently a hydrogen atom or a substituted or unsubstituted C1 To C30 alkyl group,
R 1 to R 3 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted C1 to C30 carboxyl group, a hydroxyl group or a thiol group,
n 1 is an integer of 0 to 2,
n 2 and n 3 are each an integer of 0 to 3.)
Wherein the phosphorus-containing diamine and the aromatic diamine are mixed at a weight ratio of 5:95 to 95: 5.
Wherein the alkali-soluble resin comprises a polybenzoxazole precursor comprising a repeating unit represented by the following general formulas (4) and (10).
[Chemical Formula 4]
(In the formula 4,
X 1 is a residue derived from the phosphorus-containing diamine represented by the above formula (1)
Y 1 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic group.
[Chemical formula 10]
(In the formula (10)
X 2 is a residue derived from an aromatic diamine containing at least one selected from the above formulas (8) and (9)
Y 2 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic group.
The positive photosensitive resin composition
(A ') an aromatic diamine,
Wherein the aromatic diamine comprises at least one selected from the following formulas (8) and (9).
[Chemical Formula 8]
[Chemical Formula 9]
(In the above formulas 8 and 9,
A is a single bond, -O-, -CO-, -CR 4 R 5 -, -SO 2 - or -S-, R 4 and R 5 are each independently a hydrogen atom or a substituted or unsubstituted C1 To C30 alkyl group,
R 1 to R 3 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted C1 to C30 carboxyl group, a hydroxyl group or a thiol group,
n 1 is an integer of 0 to 2,
n 2 and n 3 are each an integer of 0 to 3.)
Wherein the alkali-soluble resin (A) prepared from the phosphorus-containing diamine and the alkali-soluble resin (A ') prepared from the aromatic diamine are mixed at a weight ratio of 5:95 to 95: 5.
Wherein the alkali-soluble resin has a weight-average molecular weight (Mw) of 3,000 to 300,000 g / mol.
The positive photosensitive resin composition
With respect to 100 parts by weight of the alkali-soluble resin (A)
5 to 100 parts by weight of the photosensitive diazoquinone compound (B)
100 to 900 parts by weight of the solvent (C)
Wherein the positive photosensitive resin composition is a positive photosensitive resin composition.
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| KR1020110141439A KR101413076B1 (en) | 2011-12-23 | 2011-12-23 | Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film |
| CN2012103167182A CN103176363A (en) | 2011-12-23 | 2012-08-30 | Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film |
| US13/603,522 US9040213B2 (en) | 2011-12-23 | 2012-09-05 | Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film |
| TW101133287A TWI485523B (en) | 2011-12-23 | 2012-09-12 | Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film |
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| KR101702511B1 (en) * | 2014-06-26 | 2017-02-03 | 제일모직 주식회사 | Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and display device |
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| ATE67611T1 (en) | 1986-10-02 | 1991-10-15 | Hoechst Celanese Corp | POLYAMIDES WITH HEXAFLUOROISOPROPYLIDENE GROUPS, POSITIVE-WORKING PHOTOSENSITIVE MIXTURES CONTAINING THEM, AND RECORDING MATERIALS MANUFACTURED THEREOF. |
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